158380-76-8Relevant academic research and scientific papers
Cationic NHC-Phosphine Iridium Complexes: Highly Active Catalysts for Base-Free Hydrogenation of Ketones
Quan, Xu,Kerdphon, Sutthichat,Peters, Bram B. C.,Rujirawanich, Janjira,Krajangsri, Suppachai,Jongcharoenkamol, Jira,Andersson, Pher G.
supporting information, p. 13311 - 13316 (2020/09/22)
Novel bidentate N-heterocyclic carbene-phosphine iridium complexes have been synthesized and evaluated in the hydrogenation of ketones. Reported catalytic systems require base additives and, if excluded, need elevated temperature or high pressure of hydrogen gas to achieve satisfactory reactivity. The developed catalysts showed extremely high reactivity and good enantioselectivity under base-free and mild conditions. In the presence of 1 mol % catalyst under 1 bar hydrogen pressure at room temperature, hydrogenation was complete in 30 minutes giving up to 96 % ee. Again, this high reactivity was achieved in additive-free conditions. Mechanistic experiments demonstrated that balloon pressure of hydrogen was sufficient to form the activate species by reducing and eliminating the 1,5-cyclooctadiene ligand. The pre-activated catalyst was able to hydrogenate acetophenone with 89 % conversion in 5 min.
Substrate-Controlled Diastereoselectivity Reversal in NHC-Catalyzed Cross-Benzoin Reactions Using N-Boc-N-Bn-Protected α-Amino Aldehydes
Haghshenas, Pouyan,Quail, J. Wilson,Gravel, Michel
, p. 12075 - 12083 (2016/12/23)
The effectiveness of utilizing N-Bn-N-Boc-α-amino aldehydes in cross-benzoin reactions with heteroaromatic aldehydes is demonstrated. The reaction is both chemoselective and syn-selective, making it complementary to the anti-selective cross-benzoin reaction of NHBoc-α-amino aldehydes. Good diastereoselectivity is obtained for a variety of amino aldehydes, including nonhindered ones. A Felkin-Anh model can be used to rationalize the observed diastereoselectivity.
A facile synthesis of 1,5-disubstituted-2-aminoimidazoles: Antibiotic activity of a first generation library
Harris, Tyler L.,Worthington, Roberta J.,Melander, Christian
, p. 4516 - 4519 (2011/09/12)
An efficient synthetic route to 1,5-disubstituted 2-aminoimidazoles from readily available amino acids and aldehydes has been developed. A library of simple analogues was synthesized and several compounds were shown to exhibit notable antibiotic activity
A stereodivergent cascade imine → azomethine ylide → 1,3-dipolar cycloadditive approach to α-chiral pyrrolidines
Garner, Philip,Kaniskan, H. ümit
, p. 5181 - 5185 (2007/10/03)
Stereodivergent [3+2] cycloadditions of chiral α-amino azomethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads t
A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization
Palomo, Claudio,Oiarbide, Mikel,Garcia, Jesus M.,Gonzalez, Alberto,Pazos, Raquel,Odriozola, Jose M.,Banuelos, Patricia,Tello, Monica,Linden, Anthony
, p. 4126 - 4134 (2007/10/03)
A practical total synthesis of hapalosin, a compound with multidrug resistance-reversing activity, has been carried out using an unprecedented macrolactonization strategy. One of the features of the new approach is the straightforward and fully stereocont
Preparation of aminoepoxides from aminoaldehydes and an in situ formed halomethyl organometallic reagent
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, (2008/06/13)
In a method of preparing an aminoepoxide wherein a protected aminoaldehyde is reacted with a halomethyl organometallic reagent in an appropriate solvent at a temperature above -80 DEG C., wherein said halomethyl organometallic reagent is formed by reaction between an organometallic reagent and a dihalomethane, the improvement comprising flowing said protected aminoaldehyde into a mixing zone maintained at a temperature below 0 DEG C., also flowing said halomethyl organometallic reagent in said mixing zone for contacting in said mixing zone with said protected aminoaldehyde and also withdrawing from said mixing zone reaction products of said protected aminoaldehyde and said halomethyl organometallic reagent.
Scope and limitations of the alkylidene carbene 1,5-CH insertion reactions of α-amino acid-derived substrates
Mapitse, Renameditswe,Hayes, Christopher J
, p. 3541 - 3542 (2007/10/03)
A range of α-amino acid-derived cyclisation precursors were synthesised from suitably protected α-amino esters, via a Dibal-H/Wittig/catalytic hydrogenation strategy and each of these was subjected to alkylidene carbene-forming conditions (lithio(trimethy
Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
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Page column 41, (2008/06/13)
Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.
HETEROCYCLECARBONYL AMINO ACID HYDROXYETHYLAMINO SULFONAMIDE RETROVIRAL PROTEASE INHIBITORS
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, (2008/06/13)
Selected heterocyclecarbonyl amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.
Epoxide formation by continuous in-situ synthesis process
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, (2008/06/13)
In a method of preparing an aminoepoxide wherein a protected aminoaldehyde is reacted with a halomethyl organometallic reagent in an appropriate solvent at a temperature above -80 DEG C., wherein said halomethyl organometallic reagent is formed by reaction between an organometallic reagent and a dihalomethane, the improvement comprising flowing said protected aminoaldehyde into a mixing zone maintained at a temperature below 0 DEG C., also flowing said halomethyl organometallic reagent in said mixing zone for contacting in said mixing zone with said protected aminoaldehyde and also withdrawing from said mixing zone reaction products of said protected aminoaldehyde and said halomethyl organometallic reagent.
